Asymmetric hydroformylation- Wittig

In 2013, Wong and Landis [26] investigated an asymmetric hydroformylation-(Wittig olefination) reaction of vinyl acetate by using a chiral catalyst based on (S,S,S)-BDP at 10bar (Scheme 5.136). After optimization, several other functionalized and nonfunctionalized olefins or 1,3-dienes could be converted under these conditions. 

Scheme 5.136 Asymmetric hydroformylation-(Wittig olefination) reaction.

A multiple one-pot iterative asymmetric hydroformylation-Wittig olefination was realized with a single catalyst loading (Scheme 5.137) [26]. Noteworthy, after each run, depressurization and injection of the allyl-substituted Wittig reagent was necessary in order to avoid the undesired hydroformylation of the Wittig ylide. In this manner, the dimer and the trimer of 4-hydroxyvalerate were prepared. 

For the total synthesis of other macrocyles, such as (-)-pyrenophorol and (+)-decaestrictine via similar asymmetric hydroformylation-Wittig olefination cascade reactions, see Ref. (30). 

Risi and Burke [29, 30] synthesized (+)-patulolide C, which is a macrocyhc compound isolated from a Penicillium urticae mutant via an asymmetric sequential hydroformylation-(intramolecular Wittig olefination) reaction applying... 

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